TWI648298B - 共聚物與樹脂組合物 - Google Patents
共聚物與樹脂組合物 Download PDFInfo
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- TWI648298B TWI648298B TW107104497A TW107104497A TWI648298B TW I648298 B TWI648298 B TW I648298B TW 107104497 A TW107104497 A TW 107104497A TW 107104497 A TW107104497 A TW 107104497A TW I648298 B TWI648298 B TW I648298B
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- 239000011342 resin composition Substances 0.000 title claims description 20
- -1 polysiloxane Polymers 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 20
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 239000003999 initiator Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 15
- 238000004132 cross linking Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 229920002120 photoresistant polymer Polymers 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 239000004065 semiconductor Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
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- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CQHKDHVZYZUZMJ-UHFFFAOYSA-N [2,2-bis(hydroxymethyl)-3-prop-2-enoyloxypropyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(CO)COC(=O)C=C CQHKDHVZYZUZMJ-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- KVPKGAFEIYMIFE-UHFFFAOYSA-N 1,4-bis(tert-butylperoxy)-1,4-dimethylcyclohexane Chemical compound CC(C)(C)OOC1(C)CCC(C)(OOC(C)(C)C)CC1 KVPKGAFEIYMIFE-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- GKZPEYIPJQHPNC-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GKZPEYIPJQHPNC-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- NEDLCZSGRDXTQG-UHFFFAOYSA-N 2,6-dimorpholin-4-yl-1,7-diphenylheptan-4-one Chemical compound C1(=CC=CC=C1)CC(CC(=O)CC(CC1=CC=CC=C1)N1CCOCC1)N1CCOCC1 NEDLCZSGRDXTQG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- CJDPTOSHLLCQCD-UHFFFAOYSA-N 3,6-bis(tert-butylperoxy)-3,6-dimethylcyclohexyne Chemical compound CC(C)(C)OOC1(C)CCC(C)(OOC(C)(C)C)C#C1 CJDPTOSHLLCQCD-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- YRIBCMYGTPNNPO-UHFFFAOYSA-N C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O.C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O Chemical compound C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O.C(C)C1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O YRIBCMYGTPNNPO-UHFFFAOYSA-N 0.000 description 1
- YLQKQCFXDFSHNN-UHFFFAOYSA-N CC(C)(C#N)N=NC(=N)N Chemical compound CC(C)(C#N)N=NC(=N)N YLQKQCFXDFSHNN-UHFFFAOYSA-N 0.000 description 1
- WYEGLUNBFQDHMI-UHFFFAOYSA-N CCCCCC.C(C)(C)(C)OOC1(CCCCC1)OOC(C)(C)C Chemical compound CCCCCC.C(C)(C)(C)OOC1(CCCCC1)OOC(C)(C)C WYEGLUNBFQDHMI-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical class CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 238000012552 review Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- JSWFABOBUSWAAX-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate;2-tert-butylperoxy-2-methylpropane Chemical compound CC(C)(C)OOC(C)(C)C.CC(C)(C)OOC(=O)C1=CC=CC=C1 JSWFABOBUSWAAX-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Abstract
本揭露提供之共聚物，包括：1莫耳份的式1所示的重複單元；3至10莫耳份的式2所示的重複單元；以及5至15莫耳份的式3所示的重複單元；
其中R1係氫或甲基；R2係單鍵或C1-3伸烷基；R3為具有芳基與乙烯基的聚矽氧烷基；以及每一R4與R5各自為氫、C1-3的烷基，或具有芳基與乙烯基的聚矽氧烷基。
Description
本揭露關於共聚物，更特別關於共聚物中的重複單元結構與包含共聚物的樹脂組合物。
現有的行動裝置或顯示器均朝可撓裝置發展。大部份關於可撓裝置的研究著重基板的可撓性，但裝置中的單元是否可撓亦為裝置是否可撓的關鍵。舉例來說，在可撓裝置中的層狀物常為整片結構，若其不可撓或可撓性不佳，即使基板可撓也無法完成可撓裝置。另一方面，上述層狀物需具備高耐熱性、高穿透性、與低介電性等特性，以符合裝置需求。若層狀物可進一步感光，則可作為光阻層。如此一來，此光阻層的解析度將取決於層狀物中的組成。
綜上所述，目前亟需新的組成用於可撓裝置的層狀物，甚至作為光阻以形成可撓裝置中的圖案化單元。
本揭露一實施例提供之共聚物，包括：1莫耳份的式1所示的重複單元；3至10莫耳份的式2所示的重複單元；以及5至15莫耳份的式3所示的重複單元；
其中R1係氫或甲基；R2係單鍵或C1-3伸烷基；R3為具有芳基與乙烯基的聚矽氧烷基；以及每一R4與R5各自為氫、C1-3的烷基，或具有芳基與乙烯基的聚矽氧烷基。
本揭露一實施例提供之樹脂組合物，包括：1重量份上述的共聚物；0.01至0.1重量份的起始劑；以及0.05至0.6重量份的交聯單體。
本揭露一實施例提供之共聚物，包括：1莫耳份的式1所示的重複單元；3至10莫耳份的式2所示的重複單元；以及5至15莫耳份的式3所示的重複單元。
在一實施例中，式1中具有芳基與乙烯基的聚矽氧烷基包括：1莫耳份的式4所示的重複單元；以及0.01至1莫耳份的式5所示的重複單元。
在其他實施例中，具有芳基與乙烯基的聚矽氧烷基更包括0至1莫耳份的式6所示的重複單元。
在一實施例中，上述具有芳基與乙烯基的聚矽氧烷基的重均分子量介於2000至3000之間。若具有芳基與乙烯基的聚矽氧烷基的重均分子量過低，則無寡聚物特性。若具有芳基與乙烯基的聚矽氧烷基的重均分子量過高，則反應性差，接枝不易。
上述共聚物的形成方法可為取(1)聚合物與(2)具芳基與乙烯基的聚矽氧烷反應而成。上述(1)聚合物可由式7所示的單體、苯乙烯、與馬來酸酐聚合而成。在式7中，每一R’
各自為氫或C1-3的烷基。至於R1與R2之定義同前述，在此不贅述。
上述(2)具芳基與乙烯基的聚矽氧烷可由式8之矽烷、式9之矽烷、及視情況採用之式10的矽烷反應而成。在式8、式9、與式10中，每一R”各自為氫或C1-3的烷基。至於R6、R7、R8、與R9之定義同前述，在此不贅述。
在一實施例中，可取1重量份上述共聚物，0.01至0.1重量份的起始劑，以及0.05至0.6重量份的交聯單體，混合形成樹脂組合物。若起始劑之用量過低，則聚合度低無高分子特性。若起始劑之用量過高，則聚合度高易脆。若交聯單體的比例過低，則共聚物的交聯程度不足而無法固化。若交聯單體的比例過高，則易脆。在一實施例中，交聯單體可為丙烯酸甘油酯、二季戊四醇六丙烯酸酯、乙二醇二丙烯酸酯(ethylene glycoldiacrylate)、三乙二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、新戊二醇二丙烯酸酯、季戊四醇三丙烯酸酯(pentaerythritoltriacrylate)、季戊四醇二丙烯酸酯
(pentaerythritol diacrylate)、二季戊四醇三丙烯酸酯(dipentaerythritoltriacrylate)、二季戊四醇丙烯酸酯(dipentaerythritolacrylate)、季戊四醇六丙烯酸酯(pentaerythritolhexaacrylate)、雙酚A二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、酚醛型環氧丙烯酸酯(novolacepoxyacrylate)、二甲基丙烯酸乙二醇酯、二甲基丙烯酸二乙二醇酯、二甲基丙烯酸三乙二醇酯、二甲基丙烯酸丙二醇酯、二甲基丙烯酸1,4-丁二醇酯、二甲基丙烯酸1,6-己二醇酯、甲基丙烯酸羥乙酯、丙烯酸異辛酯、丙烯酸羥乙酯、甲基丙烯酸甲酯、甲基丙烯酸或丙烯酸等。
在一實施例中，起始劑為光起始劑，而上述樹脂組合物為光阻。上述光起始劑可為苯乙酮類如2-甲基-1-(4-(甲基硫醇基)苯基-2-嗎林基丙基酮(2-methyl-1-(4-(methylthio)phenyl)-2-morpholino-propanone)、1-羥基環己基苯基酮(1-hydroxycyclohexyl phenyl ketone)、二苯乙氧基酮(diethoxyacetophenone)、2-羥基2-甲基-1-苯基-1-丙基-1-酮(2-hydroxy-2-methyl-1-phenyl-propane-1-one)、2-甲苯基-2-(二甲基胺基)-1-[4-(嗎林基)苯基]-1-丁基-1-酮(2-benzyl-2-(dimethylamino)-1-[4-(morpholinyl)phenyl]-1-buta none)、其他合適之苯乙酮；安息香類如安息香(benzoin)、安息香甲基醚(benzoin methyl ether)、安息香二甲醚(benzyl dimethyl ketal)、其他合適之安息香；二苯基酮類如二苯基酮(benzophenone)、4-苯基二苯基酮(4-phenyl benzophenone)、羥基二苯基酮(hydroxyl benzophenone)、或其他合適之二苯基
酮；噻吨酮類如異丙基噻吨酮(isopropyl thioxanthone)、2-氯基噻吨酮(2-chlorothioxanthone)、或其他合適之噻吨酮；蒽醌類如2-乙基蒽醌(2-ethylanthraquinone)、或其他合適之蒽醌。上述之光起始劑除可單一使用外，亦可混合使用以得到較快之感光速度，比如異丙基噻吨酮混合2-甲苯基-2-(二甲基胺基)-1-[4-(嗎林基)苯基]-1-丁基-1-酮。
在一實施例中，起始劑為熱起始劑，而樹脂組合物用於形成半導體裝置中的平坦層或介電層。上述半導體裝置為可撓。在一實施例中，熱起始劑可為偶氮類如2,2’-偶氮二雙(2,4-二甲基正戊腈)(2,2’-azobis(2,4-dimethyl valeronitrile))、二甲基-2,2’-偶氮雙(2-丙酸甲酯)(dimethyl 2,2’-azobis(2-methylpropionate)、2,2-偶氮雙異丁腈(2,2-azobisiso butyronitrile，AIBN)、2,2-偶氮雙(2-甲基異丁腈)(2,2-azobis(2-methylisobutyronitrile))、1,1’-偶氮雙(環己烷-1-腈)(1,1’-azobis(cyclohexane-1-carbonitrile))、2,2’-偶氮雙[N-2-丙烯基-2-甲基丙醯胺](2,2’-azobis[N-(2-propenyl)-2-methyl propionamide])、1-[(氰基-1-甲基乙基)-偶氮基]甲醯胺(1-[(cyano-1-methylethyl)azo]formamide)、2,2’-偶氮雙(N-丁基-2-甲基丙醯胺)2,2’-azobis(N-butyl-2-methylpropionamide))、2,2’-偶氮雙(N-環己基-2-甲基丙醯胺)(2,2’-azobis(N-cyclo hexyl-2-methylpropionamide)、或其他合適之偶氮類起始劑；過氧化物類包括苯甲醯基過氧化物(benzoyl peroxide)、1,1-雙(第三丁基過氧基)環己烷(1,1-bis(tert-butylperoxy)cyclohexane)、2,5-雙(第三丁基過氧基)-2,5-二甲基環己烷
(2,5-bis(tert-butylperoxy)-2,5-dimethyl cyclohexane)、2,5-雙(第三丁基過氧基)-2,5-二甲基-3-環己炔(2,5-bis(tert-butyl peroxy)-2,5-dimethyl-3-cyclohexyne)、雙(1-(第三丁基過氧基)-1-甲基乙基)苯(bis(1-(tert-butylpeorxy)-1-methy-ethyl)benzene)、第三丁基過氧化氫(tert-butyl hydroperoxide)、第三丁基過氧化物(tert-butyl peroxide)、第三丁基過氧基苯甲酸酯(tert-butyl peroxybenzoate)、茴香基過氧化氫(cumene hydroperoxide)、環己酮基過氧化物(cyclohexanone peroxide)、二茴香基過氧化物(dicumyl peroxide)、月桂基過氧化物(lauroyl peroxide)、或其他合適之過氧化物。上述之熱起始劑除可單一使用外，亦可混合使用，端視需要而定。
由實驗可知，上述樹脂組合物在交聯硬化後形成的層狀物或圖案，具有低介電常數、小撓曲半徑、高透光度、以及高耐熱性(如在高溫下不易黃變)等特性。當上述樹脂組合物為光阻時，其形成的圖案除了上述特徵外，其解析度可達小於30μm。綜上所述，上述樹脂組合物適用於可撓裝置如行動裝置與顯示器。
為了讓本揭露之上述和其他目的、特徵、和優點能更明顯易懂，下文特舉數實施例配合所附圖示，作詳細說明如下：
實施例
製備例1
取不同莫耳份的3-(甲基丙烯醯氧)丙基三甲氧基矽烷、苯乙烯、與馬來酸酐作為共聚單體，並以上述單體之總重為基
準，取5phr的偶氮二異丁腈(AIBN)作為起始劑。將上述單體與起始劑加入75mL的甲乙酮後混合，加熱至80℃後反應4小時以形成共聚物，如式11所示。
在式11中，x、y、與z分別對應3-(甲基丙烯醯氧)丙基三甲氧基矽烷、苯乙烯、與馬來酸酐的莫耳份，且此共聚物屬無規共聚物。上述共聚物的單體用量、數均分子量、重均分子量、固含量、與25℃下的平均黏度如第1表所示。上述共聚物的數均分子量與重均分子量係由凝膠滲透層析儀(GPC，WATERS Model 600)量測，而平均黏度係由黏度儀(BROOKFIELD)在25℃下測得。
製備例2
取不同莫耳份的二苯基矽二醇、二甲氧基二甲基矽烷、與甲基乙烯基二甲氧基矽烷作為聚矽氧烷的單體。以上述單體之總莫耳數為基準，取不同莫耳%的氫氧化鋇作為鹼催化劑。在氮氣下混合單體與鹼催化劑，加熱至60℃進行溶膠-凝膠反應12小時，再減壓濃縮去除反應形成的甲醇與水以獲得聚矽氧烷，如式12所示。
在式12中，m、n、o分別對應二苯基矽二醇、二甲氧基二甲基矽烷、甲基乙烯基二甲氧基矽烷的莫耳份，且聚矽氧烷屬無規共聚物。上述聚矽氧烷的單體用量、重均分子量、與固含量如第2表所示。上述聚矽氧烷的重均分子量係由凝膠滲透層析儀(GPC)量測。
第2表
製備例3
取製備例1的共聚物與製備例2的聚矽氧烷，加入75mL的甲乙酮後加熱至60℃進行反應10小時，如式13所示。
在式13中，x、y、z、m、n、與o的定義如前述，且共聚物與聚矽氧烷基屬無規共聚物。上述共聚物與聚矽氧烷的種類與用量，以及產物的固含量、與25℃下的平均黏度如第3表所示。上述共聚物的平均黏度利用黏度儀(BROOKFIELD)
在25℃下測得。
實施例與比較例
取5重量份製備例1或3的產物、0.2重量份的Irgacure OXE 01(購於光彥貿易)作為光起始劑、與1重量份的M400(購於雙鍵化工)作為交聯單體，混合後形成樹脂組合物。將上述樹脂組合物塗佈於基板上後，以具有不同線寬圖案的測試光罩進行曝光，再顯影形成圖案，以確認圖案的解析度。此外，取上述樹脂組合物塗佈於基板上後，直接曝光硬化形成整片層狀物，以量測層狀物的介電常數(量測方法請參考Chao,H.-W.；Wong,W.-S.；Chang,T.-H.,Characterizing the complex permittivity of high-κ dielectrics using enhanced field method.Review of Scientific Instruments 2015,86(11),114701.)與撓曲半徑(量測標準為IEC 62715-6-1)。層狀物的介電常數與撓曲半徑、與光
阻圖案的解析度如第4表所示。
由上述可知，具有聚矽氧烷基的共聚物可改善樹脂組合物形成的層狀物之可撓性，並降低層狀物的介電常數。
雖然本揭露已以數個實施例揭露如上，然其並非
用以限定本揭露，任何本技術領域中具有通常知識者，在不脫離本揭露之精神和範圍內，當可作任意之更動與潤飾，因此本揭露之保護範圍當視後附之申請專利範圍所界定者為準。
Claims (9)
- 一種共聚物，包括：1莫耳份的式1所示的重複單元；3至10莫耳份的式2所示的重複單元；以及5至15莫耳份的式3所示的重複單元；其中R1係氫或甲基；R2係單鍵或C1-3伸烷基；R3為具有芳基與乙烯基的聚矽氧烷基；以及每一R4與R5各自為氫、C1-3的烷基，或具有芳基與乙烯基的聚矽氧烷基。
- 如申請專利範圍第1項所述之共聚物，其重均分子量介於5000至10000之間。
- 如申請專利範圍第1項所述之共聚物，其中具有芳基與乙烯基的聚矽氧烷基的重均分子量介於2000至3000之間。
- 如申請專利範圍第1項所述之共聚物，其中具有芳基與乙烯基的聚矽氧烷基包括：1莫耳份的式4所示的重複單元；以及0.01至1莫耳份的式5所示的重複單元，其中Ar係苯基、萘基、芘基、蒽基、菲基、或聯三伸苯基；R6係C1-3的烷基、烯基、苯基、萘基、芘基、蒽基、菲基、或聯三伸苯基；以及R7係C1-3的烷基、或苯基。
- 如申請專利範圍第4項所述之共聚物，其中具有芳基與乙烯基的聚矽氧烷基更包括：0至1莫耳份的式6所示的重複單元；其中每一R8與R9各自為C1-3的烷基。
- 一種樹脂組合物，包括：1重量份申請專利範圍第1項所述的共聚物；0.01至0.1重量份的起始劑；以及0.05至0.6重量份的交聯單體。
- 如申請專利範圍第6項所述之樹脂組合物，其中該起始劑係光起始劑，且該樹脂組合物係一光阻。
- 如申請專利範圍第6項所述之樹脂組合物，其中該起始劑係熱起始劑，且該樹脂組合物用於形成一半導體裝置中的一平坦層或介電層。
- 如申請專利範圍第8項所述之樹脂組合物，其中該半導體裝置可撓曲。
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| TW201934598A (zh) | 2019-09-01 |
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